2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester

Base Information

Chemical Name:2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester
CAS No.:756488-30-9
Molecular Formula:C₂₂H₃₂O₁₀
Molecular Weight:456.49
Hs Code.:

Synonyms:2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester

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Chemical Property of 2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester

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Technology Process of 2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester

There total 8 articles about 2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

: 756488-29-6
2-[4-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester

: 756488-30-9
2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester

Guidance literature:: With hydrogen; Pearlman's catalyst; In water; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2004.06.015

Reference yield:

: 106-44-5
p-cresol

: 756488-30-9
2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / pyridine

2: 50 percent / N-bromosuccinimide; AIBN / CCl₄ / Heating

3: 67 percent / KOtBu; 18-crown-6 / tetrahydrofuran

4: 56 percent / KOtBu / ethanol

5: KOtBu; 18-crown-6 / tetrahydrofuran

6: 73 percent / H₂ / 20 percent Pd/C / 2-methyl-propan-2-ol; H₂O

With pyridine; N-Bromosuccinimide; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; hydrogen; Pearlman's catalyst; In tetrahydrofuran; tetrachloromethane; ethanol; water; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2004.06.015

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 756488-30-9
2-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl]-malonic acid diisopropyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 3,3-dimethyldioxirane / acetone; CH₂Cl₂

2: KOtBu; 18-crown-6 / tetrahydrofuran

3: 73 percent / H₂ / 20 percent Pd/C / 2-methyl-propan-2-ol; H₂O

With 18-crown-6 ether; potassium tert-butylate; hydrogen; 3,3-dimethyldioxirane; Pearlman's catalyst; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2004.06.015